Potassium Formate → N-(4-Methyl-3-aminophenyl)-4-(4-methylpiperazinomethyl)benzamide

HRID 273300

Reaction equation

HRID 273300 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:24])[C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:25]([O-])=O.C([O-])=O.[K+]>C(O)C.[Pt]>[NH2:25][C:3]1[CH:4]=[C:5]([NH:8][C:9](=[O:24])[C:10]2[CH:11]=[CH:12][C:13]([CH2:16][N:17]3[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]3)=[CH:14][CH:15]=2)[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 2735122Potassium FormateHCID 29984087N-(4-Methyl-3-nitro-phenyl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide

Product 1

HCID 11702833N-(4-Methyl-3-aminophenyl)-4-(4-methylpiperazinomethyl)benzamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Alternatively a solution of N-(4-methyl-3-nitro-phenyl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide (60 g, 163 mmol) in ethanol 90% (300 ml) at room temperature under an atmosphere of nitrogen is treated sequentially with platinum (5%) on carbon (6.0 g) and potassium formate (68.5 g, 814 mmol). The resulting suspension is then heated at 80° C. for a period of 16 hrs. The reaction mixture is filtrated at 70° C. over a pad of Celite. Ethanol 90% (150 ml) and water (150 ml) are used to rinse the reactor. Ethanol is removed from the combined filtrates by distillation in vacuo at an external temperature 60° C. The crude product separates from the aqueous concentrate as an oil during the distillation, crystallizes upon subsequent cooling to 23° C. within 2 hrs and is filtered of with suction, washed with ethanol (200 ml) and dried in vacuo. Yield: 55 g of the title compound, 99% of theory, as yellowish crystals. (HPLC: 98.0% area).

Workup

  1. filtrationThe reaction mixture is filtrated at 70° C. over a pad of Celite
  2. washto rinse the reactor
  3. customEthanol is removed from the combined filtrates by distillation in vacuo at an external temperature 60° C
  4. concentrationThe crude product separates from the aqueous concentrate as an oil during the distillation
  5. customcrystallizes
  6. temperatureupon subsequent cooling to 23° C. within 2 hrs
  7. filtrationis filtered of with suction
  8. washwashed with ethanol (200 ml)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-097c97463e484d00b4cc6c6e7f9b5a62
Source dataset
uspto-grants-2008_11
Patent number
US07456283B2

Linked notes

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